Triethylamine → 2-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline

HRID 1417481Notes

Reaction equation

HRID 1417481 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][CH:9]([S:18][C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10][C:11]1[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=1.C(N(CC)CC)C>ClCCl.O>[S:18]1[C:19]2[NH:20][C:21]3[C:26]([C:27]=2[CH2:7][CH2:8][CH:9]1[CH2:10][C:11]1[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 542949182-[4-Hydroxy-2-(indol-2-ylthio)butyl]-4,4-dimethyl-2-oxazoline

Product 1

HCID 543591052-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazolineYield 46.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.05 ml of methanesulfonyl chloride was added to a mixture of 165 mg of 2-[4-hydroxy-2-(indol-2-ylthio)butyl]-4,4-dimethyl-2-oxazoline (prepared as described in Example 79) and 0.10 ml of triethylamine in 5 ml of dichloromethane, with stirring and ice-cooling, and stirring was continued for 30 minutes. At the end of this time, the reaction mixture was diluted with water and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was dissolved in a mixture of 5 ml of dichloromethane and 5 ml of benzene. 0.26 ml of a solution of 3M ethylmagnesium bromide in diethyl ether was then added to this mixture, with stirring, at room temperature, and stirring was continued at this temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a mixture of 30% v/v ethyl acetate in hexane as the eluent, to afford 73 mg of the title compound as a solid.

Workup

  1. temperatureice-cooling
  2. stirringstirring
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate fraction was then washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. dissolutionthe resulting residue was dissolved in a mixture of 5 ml of dichloromethane and 5 ml of benzene
  8. addition0.26 ml of a solution of 3M ethylmagnesium bromide in diethyl ether was then added to this mixture
  9. stirringwith stirring, at room temperature
  10. stirringstirring
  11. waitwas continued at this temperature for 30 minutes
  12. additionAt the end of this time, the reaction mixture was diluted with a saturated aqueous solution of ammonium chloride
  13. extractionextracted with ethyl acetate
  14. washThe ethyl acetate fraction was then washed with water
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was then removed by evaporation under reduced pressure
  17. customthe resulting residue was purified by silica gel column chromatography
  18. additiona mixture of 30% v/v ethyl acetate in hexane as the eluent

Sources & evidence

ORD record
ord-40f2f16b3ca445a6acf4979c4bf5be11
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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